Vacation rentals with a pool in San Mateo

4.95 out of 5 average rating, 134 reviews

Condo in Mountain View

Spacious Top Floor Condo Retreat

Listen to the calming sounds of all the water features throughout the property from the secluded balcony. Inside, relax in 1000 square feet of upscale surroundings that include wood floors and high quality Tempur-Pedic king mattress. Later, head for the ground-floor pools and hot tub. 1000 sq ft of space on the top floor. Queen size adjustable firmness air mattress with clean beddings available upon request to be set up in the living room. You will be able to access the entire unit, 2 Swimming pools, and the hot tub. I will be available by text, phone or email throughout the stay. The quiet and beautiful setting is surrounded by trees. Within walking distance to CalTrain station, San Antonio shopping center, and Whole Foods, Trader Joe, movie theater plus numerous boutiques. Major tech companies located nearby include G00gle and Faceb00k. Stanford University is within a 10 minute drive. A short 5-10 minute walk to the Cal Train stop but the unit is not impacted by any train noise. The bus stop is conveniently around the corner to take you to Downtown Castro Street or Stanford University and beyond.

4.93 out of 5 average rating, 155 reviews

A serene swimming pool reflects the clear blue sky, surrounded by lush landscaping. Natural stone steps lead to the house, flanked by vibrant foliage and small waterfalls, creating a tranquil retreat.

Home in Portola Valley

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

4.99 out of 5 average rating, 330 reviews

A tranquil pool area is surrounded by lush greenery and rustic wooden structures. The clear water reflects the trees and sunlight above. A wooden deck offers space for relaxation, while adjacent seating arrangements and a grill provide options for outdoor enjoyment.

Guesthouse in Woodside

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

4.97 out of 5 average rating, 249 reviews

Guesthouse in Oakland

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated 82F May 1st-Oct. 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 582 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cozy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mile from Berkeley/Oakland, 50 mile from Napa Valley Wineries. Perfectly located in a quiet, safe and green neighborhood: 0.8 mile from Walnut Creek BART station and 1 mile from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big and is good for couples, solo and business travelers.

4.95 out of 5 average rating, 199 reviews

A tranquil infinity pool is framed by lush greenery, with mountains visible in the background under a clear blue sky. A large umbrella provides shade over a pair of lounge chairs, accompanied by a small side table. Paved stone surrounds the pool area.

Guest suite in Fairfax

Mountain View Retreat

Exclusive garden level retreat in the peaceful coastal hills of Marin County. Private entry French doors open to expansive decks, magnificent views, large infinity pool, hot tub, & gas barbecue grill. 2 Flat-screen cable TV's, with premium channels, (living room & bedroom). High-speed Wi-Fi internet throughout. Central location for easy access to San Francisco, Sonoma/Napa wine country, Pacific Coast beaches, spectacular Redwood forests, and endless miles of hiking & biking trails.

4.96 out of 5 average rating, 163 reviews

Guesthouse in San Rafael

Hillside Oasis Btwn SF, Napa w/ Big Views + Pool!

Welcome to your retreat! Drive through the gate to a peaceful setting. Sunset from your private deck in the hills above San Rafael. It's like a treehouse but with no stairs! Stay home all day (guests love the bed!) or visit the adorable towns and famous hikes of Marin. 45 mins to Napa/Sonoma or 15 min to San Francisco - experience the best of the Bay from here. Happy to help you plan. Separate building from main house. TV: Netflix, Hulu, Disney+ & more! Pool heated May - August.

Farm stay in Walnut Creek

A swimming pool is set against the backdrop of a two-story house, surrounded by lush greenery. Poolside seating is available with lounge chairs positioned for relaxation. A hot tub can be seen nearby, nestled within the vibrant garden foliage.

4.99 out of 5 average rating, 559 reviews

Garden Oasis Studio with Spa and Pool Walnut Creek

Former Plus-rated studio. How about a rejuvenating get-away with pool and hot tub? Picture window overlooking the garden. Sunbathe poolside. Watch TV from a comfy bed before falling into a restful sleep. Complimentary beverage for 3+ nights. After 10 stays, $100 credit. Deep cleaned. 2 separate units off same foyer; but no shared walls. Private locked unit door. Shared access to spa/pool (9am-11pm) for overnight guests only. 27 stairs outside, 3 inside. Host lives upstairs.

Guesthouse in Walnut Creek

A swimming pool is surrounded by a concrete deck, featuring several colorful floatation devices. Two wicker chairs and a small table are positioned near the edge, providing a space to relax amidst green trees in the background under a clear blue sky.

4.95 out of 5 average rating, 109 reviews

The Willow Cottage

Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

Guesthouse in Almaden Valley

The outdoor pool is framed by a spacious deck, featuring a stone cabana with large glass doors. Surrounding greenery adds a natural touch, while clear blue skies create a serene atmosphere. Sun loungers are positioned nearby, inviting relaxation by the refreshing water.

4.97 out of 5 average rating, 974 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

4.93 out of 5 average rating, 366 reviews

An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.

Home in Los Altos

Silicon Valley Luxury I Sauna, Hot Tub, Pool

Secluded, peaceful 1,500 sq. ft. hillside escape for couples, nature lovers & business travelers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access & abundant wildlife. Features a fully equipped kitchen, pool table, fireplace, sauna, saline hot tub & pool. Fast fiber-optic WiFi for work & streaming. Prime location: I-280 (1.5 mi), Los Altos dining/shopping (3 mi), Mountain View (5 mi), Cupertino (8 mi), Palo Alto (9 mi).

4.99 out of 5 average rating, 224 reviews

A serene outdoor space features a shimmering salt water pebble sheen lap pool surrounded by lush greenery. Tropical palm trees and colorful plants frame the pool area, with lounge seating and an umbrella providing shaded relaxation options. The inviting atmosphere is complemented by natural light filtering through the trees.

Guesthouse in Sunnyvale

Lux Villa, sunny deck w fire pit, private retreat

• Indoor/outdoor living, private deck, outdoor seating • Has it's own air conditioning & heating units controlled by a Nest thermostat (no shared ducts) • Ventilated with an air filtration system • Eco cleaners and disinfected • Self check-in & check-out • Upgraded high speed WiFi • Gas fireplace • High ceilings • Gourmet kitchen • Aroma & sound therapy • Walk-in shower w/heated towel rack • Sunny private deck seating w fire pit

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for San Mateo rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 104 reviews

A cozy outdoor space is illuminated by string lights, creating a warm ambiance. A small round table sits in the center, surrounded by chairs. Nearby, a garden cottage and trees provide a natural backdrop, enhancing the serene atmosphere of the backyard.

Home in Oakland

Summer-house/OASIS on quiet street in ROCKRIDGE!

MartinRating, 5 stars4 weeks ago

Very homey and welcoming. Family enjoyed celebrating time together in all spaces of the house, especially the back patio where our young child made believe on the well-designed pirate ship. Friendly, kind host. We walked to adorable Rockridge and BART many times. Highly recommended.

4.73 out of 5 average rating, 26 reviews

A small round table is positioned between two high-backed chairs, providing a cozy seating area. Above the table, a flat-screen television displays an image of the Golden Gate Bridge, complemented by a decorative vase on the table.

Home in San Mateo

Charming English Oasis

IgorRating, 5 stars3 months ago

I really enjoyed my two-week stay at Will's place! The apartment was clean and cozy, and the building appeared modern and new. I noticed a few reviews mentioning minor issues, but honestly, I had a great experience. The location is good – you can easily walk to a bakery, supermarket, and restaurants. Will was a great host, always available, friendly, and helpful with any questions. I recommend Will's place to anyone visiting the city – it's a great choice!

4.8 out of 5 average rating, 210 reviews

A large in-ground pool is set in a landscaped garden, surrounded by a mix of greenery and fencing for safety. The smooth pool surface reflects the blue sky, while a covered area with red seating is visible in the background.

Home in Willow Glen

Beautiful Large 4BR Home with POOL

NatashaRating, 5 stars2 days ago

Immaculately maintained, spacious property. Very relaxing. Close to all the necessary shops. Well equipped for families.

4.92 out of 5 average rating, 207 reviews

An outdoor area features a turquoise umbrella shading a round dining table with five chairs, positioned near a swimming pool. A gas grill is visible beside the table. Colorful pool floats are arranged in the clear water, while a tree offers additional shade in the background.

Home in Concord

Pool, Hot tub, Napa, SFO Clean

DonRating, 5 stars1 week ago

The place was clean and beautiful. We needed a home away from home while construction was going on at our place. And found it here.

4.88 out of 5 average rating, 16 reviews

A lush landscape filled with vibrant flowers surrounds a serene cottage. The charming home features a welcoming porch, offering a natural view of the hillside greenery and blooming gardens, enhancing the tranquil outdoor setting.

Home in Tiburon

Unreal Beachfront Marin Getaway!

JoeRating, 5 stars1 month ago

A group of lifelong friends and I meet once a year for a long weekend to catch up, decompress, and spend time together. We chose San Francisco this year and after hunting on AirBnB we stumbled across this estate on JAR Farms. The host Nikki was proactive, helpful, and responsive. We arrived on Wednesday and drove to thru the gate into a lush oasis. The pictures on the listing didn't do the property justice. We arrived at the guest house to a welcome gift of wine, local honey, and snacks. We were a group of 6 adults and the guest house was cozy yet a perfect size for a reunion of friends. We were given a tour of the property showing us the boat house/beach, grand staircase to the bay overlook, the pool house (pool and hot tub), gardens, bee hives, and the many trails on the property. The mornings we hiked Monahan Trail at the adjacent Old St. Hillary's Preserve. In the afternoons we enjoyed the hot tub and a nice bbq dinner. Perfect weekend! HIGHLY recomended. Will be returning!

4.89 out of 5 average rating, 55 reviews

An inviting outdoor space features a saltwater pool surrounded by lush greenery and lounge seating. A covered area displays comfortable seating and decorative hats, with towels neatly arranged in baskets nearby. The bright sky enhances the serene atmosphere of the garden retreat.

Home in Menlo Park

Mission style, w. Pool, Hot tub, walk to downtown

MorganRating, 5 stars6 months ago

Sara and Nic were gracious and very responsive hosts. Their home is spacious, clean, comfortable, and suited our needs perfectly. The outdoor space also looked wonderful but we didn't use it much because our visit was during winter.

5 out of 5 average rating, 72 reviews

An outdoor space is adorned with colorful lanterns and a vibrant flag, creating a lively atmosphere. A hot tub is visible alongside a small pool featuring an illuminated ring. Comfortable seating areas are surrounded by tropical plants, enhancing the welcoming environment for guests.

Home in Oakland

Cactus House & Suite: 4 bedroom 3 bathroom

AlbertRating, 5 stars9 months ago

Had an excellent stay with our family. Will is one of the best airbnb hosts we have ever had and would stay again at this home or any other home he hosts without hesitation. The cactus home is luxurious and has amazing amenities like heated bathroom floors, great outdoor space with pool and hot tub, and a well equipped kitchen.

5 out of 5 average rating, 31 reviews

An outdoor space features a swimming pool surrounded by lounge chairs and a wooden dining table with umbrellas for shade. Lush greenery and hills are visible in the background, providing a serene atmosphere. The patio has large tiles to create a spacious walkway.

Home in San Anselmo

Hill Top Spa Retreat

SreejitRating, 5 stars2 weeks ago

Job’s place is a true gem. The pictures dont do the place justice. Its beautfully decorated with excellent amenites both in and outside the house. The view is unbeatable and the locaion is so peaceful. The pool house was one of the top highlights. Job was a very helpful host and super responsive to our requests. I would definitely come back here. Thank you Job for sharing your place with us

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Condo rentals with a pool

Condo in Downtown Oakland

A modern living space presents a deep-seated couch paired with a stylish coffee table, set against a backdrop of vibrant artwork. Natural light filters in through a window, while a door leads to the outside. A dining area is visible in the corner.

4.92 out of 5 average rating, 293 reviews

Lakeside Retreat (w/ private parking)

DennisRating, 5 stars3 weeks ago

Very responsive and helpful host… would definitely go back and stay there when visiting the Bay Area again

4.94 out of 5 average rating, 31 reviews

A spacious living room is highlighted by a cozy gray sofa and a circular coffee table placed on a light area rug. A ceiling fan is positioned above, and a decorative piece is displayed on the wall. Natural light filters in from large windows, and a fireplace is present.

Condo in Walnut Creek

Downtown Modern Living Condo!

ColleenRating, 5 stars3 days ago

It was a quiet complex and the house was a great option for us for a couple nights. Would stay again.

A modern sectional sofa with light upholstery is positioned in the foreground, featuring a spacious chaise lounge. The room is bright, with high ceilings and a circular pendant light hanging above. A staircase with a black railing leads to the loft area in the background.

Condo in San Mateo

5 out of 5 average rating, 3 reviews

Luxury loft by the water

SondraRating, 5 stars1 month ago

As a solo female traveler in town for business, this place was great. Short distance to the office but had everything you needed for working remote. Loved the kitchen set up and had everything I needed to make breakfast and dinner. The bed was so comfortable, I didn’t want to leave! My rav4 fit well in the garage. The walking path outside was great for either starting your day or winding down.

Condo in Mission District

A cozy living area features a deep blue sofa and a round coffee table atop a soft area rug. Natural light filters through multiple windows, illuminating various plants that enhance the inviting space. A small accent chair and a decorative stool add to the inviting arrangement.

4.96 out of 5 average rating, 23 reviews

Art Deco Mission Flat

ShawnRating, 5 stars3 months ago

Lyssette’s lovely flat was exactly as described & very comfortable. It is in the heart of the mission district with so many restaurants & neat shops nearby. Highly recommended!

4.67 out of 5 average rating, 12 reviews

The lake view features multiple sailboats gliding across the water, with a backdrop of tall buildings and a clear sky. Below, a vibrant market scene displays food stalls under palm trees, with a retro sign indicating a nearby venue offering breakfast and lunch.

Condo in Grand Lake

Cozy condo by the lake

GaryRating, 5 stars1 month ago

The accommodations were nice and the area was quiet. It was a short walk to shops, restaurants, a movie theater and a 5 minute drive to a supermarket. It was a short walk to the lake which had a circumferential walking path. We particularly liked the locked parking garage. We will definitely come back.

4.94 out of 5 average rating, 17 reviews

This two-story condo is set within landscaped grounds, featuring a mix of grassy areas and walkways. The exterior is highlighted by a combination of neutral-colored walls and wood accents. A small patio area can be seen at the side, accompanied by trees and shrubbery.

Condo in San Jose

Charming 2 bedroom 2 story condo - No smoking

JesusRating, 5 stars2 weeks ago

We had a great stay at Mayela’s place! Communication was smooth and helpful she provided clear instructions and useful information before our arrival. The home was clean, comfortable. Parking instructions were very helpful as well. Overall, a great experience.